| Identification | More | [Name]
Diphenylmethane | [CAS]
101-81-5 | [Synonyms]
BENZYLBENZENE
BENZYLPHENYL
DIPHENYLMETHANE
DITANE
METHYLENEDIBENZENE
(phenylmethyl)-benzen
1,1’-methylenebis(benzene)
1,1’-methylenebis-benzen
1,1’-methylenebisbenzene
1,1’-methylenebis-Benzene
1,1'-Dimethylenebis(benzene)
1,1-Methylenebisbenzene
ai3-00748
ai3-28021-x
Artificialgeranium
Benaylbenzene
Benzene, (phenylmethyl)-
Benzene, 1,1'-methylenebis-
Benzene, benzyl-
Benzene,1,1’-methylenebis- | [EINECS(EC#)]
202-978-6 | [Molecular Formula]
C13H12 | [MDL Number]
MFCD00004781 | [Molecular Weight]
168.23 | [MOL File]
101-81-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White low melting solid | [Melting point ]
22-24 °C (lit.) | [Boiling point ]
264 °C (lit.) | [density ]
1.006 g/mL at 25 °C(lit.)
| [vapor density ]
5.79 (vs air)
| [vapor pressure ]
<1 mm Hg ( 77 °C)
| [refractive index ]
n20/D 1.577(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
Soluble in ethanol, ether, benzene and chloroform. | [form ]
Low Melting Solid | [pka]
33.5(at 25℃) | [color ]
Colorless to pale yellow | [Specific Gravity]
1.006 | [Odor]
at 10.00 % in dipropylene glycol. sweet green wet plastic geranium | [explosive limit]
0.69-8.66%(V) | [Odor Type]
green | [Water Solubility ]
14.1mg/L(25 ºC) | [FreezingPoint ]
24.0 to 26.0 ℃ | [Merck ]
14,3328 | [BRN ]
1904982 | [Dielectric constant]
2.6（26℃） | [LogP]
4.140 | [CAS DataBase Reference]
101-81-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Diphenylmethane(101-81-5) | [EPA Substance Registry System]
101-81-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN3077 | [WGK Germany ]
2
| [RTECS ]
DA4976500
| [Autoignition Temperature]
905 °F | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29029090 | [Hazardous Substances Data]
101-81-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 2250 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Aluminum chloride-->Zinc chloride-->amalgam-->Chlorodiphenylmethane-->Benzene, 1-(1,1-dimethylethyl)-4-(phenylmethyl)--->3-ETHYL-2,4-PENTANEDIONE | [Preparation Products]
β-Estradiol-->2-(4-CHLOROPHENYL)-3-METHYLBUTYRONITRILE-->α-phenyl-2-p-tolylethylamine-->Azelastine-->Bromodiphenylmethane-->BLASTICIDIN S-->Polymethylene polyphenyl polyisocyanate-->2,2-Diphenylacetic acid-->diphenylmethyllithium-->4-FLUORO-4'-NITROBENZOPHENONE-->4,4'-DDM-->2-Methyl-1,3-cyclopentanedione-->1,1'-(Methylene-di-4,1-phenylene)bis[2-hydroxy-2-methyl-1-propanone]-->(2-(4-vinylphenyl)ethene-1,1,2-triyl)tribenzene-->DIPHENYLMETHANE-4,4'-DICARBOXYLIC ACID |
| Questions And Answer | Back Directory | [Definition]
Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH2Ph2). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as benzhydryl, and it is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride.
| [Uses]
Diphenylmethane is widely used in the synthesis of luminogens for aggregation-induced emission (AIE).
It is used in the preparation of a polymerization initiator, diphenylmethyl potassium (DPMK).
It is one of the precursors in the synthesis of a dendrimeric polycyclic aromatic hydrocarbon (PAH), hexakis[4-(1,1,2-triphenyl-ethenyl)phenyl]benzene.
| [Application]
The main application of diphenylmethane includes widely used in the synthesis of luminogens for aggregation-induced emission (AIE) and used in the preparation of a polymerization initiator, diphenylmethyl potassium (DPMK). It is one of the precursors in the synthesis of a dendrimeric polycyclic aromatic hydrocarbon (PAH), hexakis [4-(1,1,2-triphenyl-ethenyl) phenyl] benzene.
| [Synthesis]
The classical synthesis of Diphenylmethane (DPMK) is the indirect metallation via potassium naphthenide. n-Butyllithium (n-BuLi) solution (1.6 M in hexanes) and sec-butyllithium (sec-BuLi) solution (1.4 M in cyclohexane) were diluted and ampoulized on a high vacuum line. Lithium chloride (99.999%, LiCl,) was dried at 130 °C for 2 days and then diluted to the target concentration in THF and ampoulized under a reduced pressure of 10-6 mm Hg. Sodium (NaNaph) and potassium naphthalenide (K-Naph) were prepared by the reaction of the corresponding metal with naphthalene in THF at room temperature for 48 h. Diphenyl methyl potassium (DPMK) was prepared by the reaction of K-Naph with diphenylmethane in THF under high vacuum conditions at room temperature for 72 h. The concentration of DPMK was determined by titration using octyl alcohol and used for anionic polymerization. All initiators were sealed off under high vacuum into ampoules with break seals and stored at -30 °C.
|
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to pale yellow low melting solid | [Occurrence]
Has apparently not been reported to occur in nature. | [Preparation]
By interaction of benzyl chloride and benzene in the presence of an acid cata lyst. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 91, p. 5663, 1969 DOI: 10.1021/ja01048a053
Chemical and Pharmaceutical Bulletin, 27, p. 2405, 1979 DOI: 10.1248/cpb.27.2405
The Journal of Organic Chemistry, 57, p. 2143, 1992 DOI: 10.1021/jo00033a041 | [Metabolism]
Diphenylmethane is hydroxylated in the rabbit and some 15% of the dose is excreted as 4-hydroxydiphenylmethane, which is largely (80-90%) in the free state. Neither the hydrocarbon nor its metabolite is oestrogenic. This reaction also occurs in the dog (Williams, 1959). | [Purification Methods]
Sublime it under vacuum, or distil it at 72-75o/0.4mm. Recrystallise it from cold EtOH. It has also been purified by fractional crystallisation from the melt. [Armarego Aust J Chem 13 95 1960, Beilstein 5 II 498, 5 IV 1841.] |
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